At least in relative terms, it hasn’t been a great offseason for Scott Boras and his quartet of star clients.

Boras’ gang of four — Matt Chapman, Cody Bellinger, Blake Snell and Jordan Montgomery — have seen their respective markets progress at a glacial pace. Chapman landed a deal with the San Francisco Giants, Bellinger eventually latched back on with the Chicago Cubs and Snell is reportedly in agreement with Chapman’s Giants, according to multiple reports. The only one left on the market is Montgomery, whose signing doesn’t appear imminent at the moment.

In the case of Chapman, Bellinger and Snell, their reported contract figures don’t even come close to projections. Snell is reportedly signing what’s technically a two-year deal with the Giants that could be worth $62 million. However, the pact includes an opt-out after the 2024 season that essentially means Snell will probably be back on the market next winter if he can come close to replicating his 2023 performance that won him the National League Cy Young Award with the San Diego Padres.

It’s borderline comical to look back at MLB Trade Rumors’ free agent contract predictions for the Boras four and compare it to what each received.

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Chapman: six years, $150 million (actual contract: three years, $54 million)
Snell: seven years, $200 million (actual contract: two years, $62 million with an opt-out)
Bellinger: 12 years, $264 million (actual contract: three years, $80 million with two opt-outs)
Montgomery: six years, $150 million (still unsigned)

Suffice it to say, as we sit here on March 19 with Opening Day a little more than a week away, Montgomery probably doesn’t have a six-year, $150 million offer on the table. None of this is to besmirch the work done by the guys at MLB Trade Rumors. The actual deals are going to fall way short of all prognostications — most notably Boras’ desires and demands.

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At this point, it’s probably safe to assume whatever deal Montgomery signs will look similar to Snell’s at least in the way it’s structured. Snell is the better pitcher and his compensation will reflect as much. But the two left-handers are both 31 years old, so the comp is right there for Montgomery. He’ll probably sign a short-term deal with opt-outs at every possible step.

Let’s just say something like two years and $55 million with an opt-out after Year 1. We’ve certainly heard plenty of reports and speculation about the Red Sox and Montgomery. Boston has confirmed its interest in the 2023 World Series champion.

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The Red Sox, specifically CEO Sam Kennedy, has also admitted there are financial parameters within which chief baseball officer Craig Breslow is working. Presumably, that includes staying under the competitive balance tax (CBT). According to Red Sox Payroll, Boston currently is at $213 million after the recent Brayan Bello extension. That doesn’t include the potential big league money for players like Roberto Perez, Lucas Luetge or C.J. Cron, who would see notable pay increases — compared to the league minimum — if and when they’re added to the major league roster. If Montgomery is making anything in the neighborhood of our imagined $27.5 million annual salary, it will require additional moves to stay under the CBT — assuming that’s even the financial North Star.

Assuming those sorts of contractual gymnastics were necessary, Montgomery at a discounted rate and shorter money makes him more palpable, at least in a vacuum. The Red Sox haven’t been keen on giving out long-term contracts, especially to starting pitchers over the age of 30. Montgomery for two or three years is far more appetizing than for six or seven years.

Here’s the big problem, though: That’s the case for a lot of teams. If the price comes down for one team, it comes down for all teams. Weirdly, Montgomery’s market actually increases if the parameters have truly changed. All of a sudden, the idea of adding a left-handed innings eater who was an absolute stud in the playoffs last year comes back on the radar for even more of the league. Take the Yankees, for example. If Gerrit Cole is going to miss extended time, they are familiar with Montgomery and might be more likely to take on any risk if they know it might just be for the 2024 season. The same could be said for a team like the Houston Astros. The Texas Rangers, the team Montgomery just helped win a World Series, could get creative to find a way to make it work on a shorter deal despite their own financial constraints. A team like the St. Louis Cardinals, also familiar with Montgomery, could be an option now, too.

The Red Sox obviously believe they can exceed expectations in 2024. However, looking at World Series odds, Boston’s 65-1 number is longer than 20 teams in the majors right now. A lot of those clubs could financially stomach a shorter-term deal, and if they were to contend for a World Series, that’s probably even more important to a player like Montgomery when looking at a shorter deal. It gives him a great chance to further cement himself as a big-game player who could opt out after the season and do this all over again.

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If the Red Sox do miss out on Montgomery this offseason despite the obvious fit, a Snell-like deal could mean they’ll get another crack at him soon. If it doesn’t make sense to do it now, the team’s hope should be that there’s enough improvement in 2024 to make them legitimate suitors once again as soon as Montgomery — or any other front-line pitcher — becomes available again.

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